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In the crystal structure of the title compound, C6H10N3+·Br·C6H9N3·H2O, the asymmetric unit contains a 2-amino-4,6-di­methyl­pyrimidinium cation, a Br anion, a neutral 2-amino-4,6-di­methyl­pyrimidine mol­ecule and a water mol­ecule. Each neutral base molecule is paired with another inversion-related molecule through N—H...N hydrogen bonds to form dimers, and these are linked to one another through water-mediated hydrogen bonds, generating a supramolecular ribbon. The cations also pair with one another through N—H...N hydrogen bonds. The cation pairs are stacked on top of the neutral pairs. The Br anion also takes part in hydrogen bonding (N/O—H...Br).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007597/ci6355sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007597/ci6355Isup2.hkl
Contains datablock I

CCDC reference: 239135

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.136
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ?
Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.98 Deg. PLAT057_ALERT_3_B Correction for Absorption Required RT(exp) ... 1.24
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: MolEN (Fair, 1990); cell refinement: MolEN; data reduction: MolEN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON97 (Spek, 1997).

2-amino-4,6-dimethylpyrimidinium bromide 2-amino-4,6-dimethylpyrimidine monohydrate top
Crystal data top
C6H10N3+·Br·C6H9N3·H2OZ = 2
Mr = 345.25F(000) = 356
Triclinic, P1Dx = 1.410 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.002 (4) ÅCell parameters from 25 reflections
b = 9.438 (8) Åθ = 3–25°
c = 12.658 (6) ŵ = 2.53 mm1
α = 79.56 (5)°T = 293 K
β = 83.85 (4)°Plate, colourless
γ = 82.98 (6)°0.35 × 0.35 × 0.25 mm
V = 813.4 (9) Å3
Data collection top
Enraf-Nonius CAD-4
diffractometer
2095 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.0°, θmin = 2.2°
ω/2θ scansh = 08
Absorption correction: ψ scan
(North et al., 1968)
k = 1111
Tmin = 0.439, Tmax = 0.531l = 1415
3101 measured reflections2 standard reflections every 60 min
2843 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.0646P)2 + 0.8382P]
where P = (Fo2 + 2Fc2)/3
2843 reflections(Δ/σ)max = 0.002
187 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.57 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N110.6470 (5)0.0555 (4)0.7223 (3)0.0389 (11)
N120.5696 (6)0.1002 (4)0.8791 (3)0.0508 (14)
N130.5505 (5)0.1434 (4)0.8841 (3)0.0396 (11)
C120.5885 (6)0.0334 (4)0.8289 (3)0.0367 (12)
C140.5758 (6)0.2755 (4)0.8302 (4)0.0402 (14)
C150.6414 (6)0.3013 (5)0.7217 (4)0.0451 (16)
C160.6747 (6)0.1887 (5)0.6665 (3)0.0440 (14)
C170.7351 (8)0.1979 (6)0.5490 (4)0.065 (2)
C180.5276 (8)0.3967 (5)0.8942 (4)0.0595 (17)
N10.0883 (5)0.3243 (4)0.8157 (3)0.0427 (11)
N20.0040 (6)0.2064 (4)0.9853 (3)0.0505 (13)
N30.0698 (5)0.0678 (4)0.8529 (3)0.0388 (11)
C20.0540 (6)0.1991 (4)0.8824 (3)0.0380 (12)
C40.1306 (6)0.0610 (5)0.7508 (3)0.0403 (14)
C50.1721 (6)0.1831 (5)0.6777 (4)0.0470 (14)
C60.1467 (6)0.3142 (5)0.7129 (4)0.0455 (16)
C70.1796 (8)0.4529 (6)0.6380 (4)0.0670 (19)
C80.1529 (8)0.0857 (5)0.7183 (4)0.0566 (17)
O1W0.0647 (7)0.4027 (4)0.1283 (4)0.0820 (18)
Br10.30561 (8)0.25741 (6)0.35557 (4)0.0621 (2)
H5A0.662300.394500.687200.0540*
H110.667300.017400.689000.0470*
H12A0.533200.116100.946900.0610*
H12B0.593800.171200.844100.0610*
H17A0.793300.104900.535100.0960*
H17B0.826700.267800.527600.0960*
H17C0.624000.227000.508800.0960*
H18A0.417800.377000.944700.0890*
H18B0.498200.486000.846200.0890*
H18C0.636100.404300.932400.0890*
H2A0.029700.129201.029600.0600*
H2B0.015900.288301.007400.0600*
H50.215900.176900.606500.0560*
H7A0.057400.505100.620600.1000*
H7B0.253000.431700.573200.1000*
H7C0.249500.510600.672300.1000*
H8A0.147800.158900.781700.0850*
H8B0.274800.099800.677000.0850*
H8C0.050200.092200.675400.0850*
H1A0.132900.372500.176100.08 (2)*
H1B0.008400.477400.142100.10 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N110.042 (2)0.0415 (19)0.0333 (18)0.0032 (15)0.0034 (15)0.0115 (15)
N120.078 (3)0.038 (2)0.035 (2)0.0023 (19)0.0029 (18)0.0099 (16)
N130.044 (2)0.039 (2)0.0373 (19)0.0059 (15)0.0010 (15)0.0109 (16)
C120.036 (2)0.039 (2)0.036 (2)0.0006 (17)0.0047 (17)0.0103 (18)
C140.034 (2)0.039 (2)0.049 (3)0.0035 (17)0.0052 (18)0.0107 (19)
C150.045 (3)0.043 (2)0.046 (3)0.010 (2)0.005 (2)0.000 (2)
C160.039 (2)0.056 (3)0.034 (2)0.004 (2)0.0055 (18)0.001 (2)
C170.079 (4)0.075 (4)0.035 (3)0.006 (3)0.007 (2)0.003 (2)
C180.074 (3)0.041 (3)0.069 (3)0.015 (2)0.003 (3)0.023 (2)
N10.045 (2)0.0348 (19)0.046 (2)0.0012 (15)0.0094 (17)0.0002 (16)
N20.086 (3)0.0323 (18)0.034 (2)0.0067 (18)0.0062 (19)0.0066 (15)
N30.043 (2)0.0382 (19)0.0368 (19)0.0050 (15)0.0035 (15)0.0099 (15)
C20.040 (2)0.037 (2)0.037 (2)0.0016 (18)0.0092 (18)0.0044 (18)
C40.034 (2)0.051 (3)0.037 (2)0.0018 (19)0.0034 (18)0.012 (2)
C50.040 (2)0.063 (3)0.035 (2)0.002 (2)0.0028 (19)0.003 (2)
C60.041 (2)0.050 (3)0.041 (3)0.002 (2)0.007 (2)0.004 (2)
C70.073 (4)0.061 (3)0.053 (3)0.004 (3)0.001 (3)0.016 (3)
C80.070 (3)0.056 (3)0.049 (3)0.010 (2)0.005 (2)0.026 (2)
O1W0.132 (4)0.048 (2)0.072 (3)0.001 (2)0.024 (3)0.023 (2)
Br10.0760 (4)0.0533 (3)0.0591 (4)0.0077 (2)0.0149 (3)0.0197 (2)
Geometric parameters (Å, º) top
O1W—H1B0.80C16—C171.492 (6)
O1W—H1A0.80C15—H5A0.93
N11—C161.351 (6)C17—H17C0.96
N11—C121.354 (5)C17—H17A0.96
N12—C121.320 (5)C17—H17B0.96
N13—C121.339 (5)C18—H18C0.96
N13—C141.331 (6)C18—H18B0.96
N11—H110.86C18—H18A0.96
N12—H12B0.86C4—C81.500 (7)
N12—H12A0.86C4—C51.381 (7)
N1—C61.338 (6)C5—C61.375 (7)
N1—C21.353 (5)C6—C71.498 (7)
N2—C21.334 (5)C5—H50.93
N3—C41.327 (5)C7—H7B0.96
N3—C21.346 (5)C7—H7C0.96
N2—H2A0.86C7—H7A0.96
N2—H2B0.86C8—H8C0.96
C14—C181.504 (7)C8—H8A0.96
C14—C151.388 (7)C8—H8B0.96
C15—C161.359 (7)
Br1···N12i3.537 (5)C17···C5x3.594 (8)
Br1···O1W3.471 (6)C18···C18xi3.551 (8)
Br1···N11i3.248 (5)C2···H1Biii2.9948
Br1···H8Cii3.1894C4···H2Avii3.0869
Br1···H17C3.0631C6···H1Biii2.9624
Br1···H12Bi2.7874C7···H1Biii3.0952
Br1···H53.1425C7···H17Bv3.0551
Br1···H7Aiii3.2037C12···H12Aviii3.0840
Br1···H11i2.4126C14···H12Aviii3.0145
Br1···H1A2.6789C18···H12Aviii3.0663
Br1···H8Bi3.1478H1A···H12Bi2.5533
O1W···N2iv2.926 (6)H1A···Br12.6789
O1W···N1iii2.848 (6)H1B···C2iii2.9948
O1W···Br13.471 (6)H1B···N1iii2.0546
O1W···H2Biv2.1815H1B···C6iii2.9624
O1W···H8Aii2.8862H1B···C7iii3.0952
O1W···H18Cv2.8945H2A···N3vii2.1872
N1···C143.408 (6)H2A···C4vii3.0869
N1···O1Wiii2.848 (6)H2A···H8Avii2.4961
N2···O1Wvi2.926 (6)H2B···O1Wvi2.1815
N2···N3vii3.045 (6)H5···H8B2.5995
N3···N2vii3.045 (6)H5···Br13.1425
N11···Br1i3.248 (5)H5···H7B2.4063
N12···N13viii2.993 (6)H5A···H18B2.4512
N12···Br1i3.537 (5)H7A···Br1iii3.2037
N13···N12viii2.993 (6)H7B···H52.4063
N1···H1Biii2.0546H8A···O1Wii2.8862
N3···H2Avii2.1872H8A···H2Avii2.4961
N13···H12Aviii2.1341H8B···Br1i3.1478
C2···C14ix3.447 (7)H8B···H52.5995
C4···C16ix3.479 (7)H8C···Br1ii3.1894
C4···C123.421 (7)H11···Br1i2.4126
C5···C16ix3.494 (7)H11···H12B2.2715
C5···C17ix3.594 (8)H11···H17A2.2297
C5···C163.513 (7)H12A···N13viii2.1341
C6···C143.443 (7)H12A···C12viii3.0840
C6···C15ix3.544 (7)H12A···C14viii3.0145
C6···C153.464 (7)H12A···C18viii3.0663
C7···C153.561 (8)H12A···H18Aviii2.5949
C12···C43.421 (7)H12B···H1Ai2.5533
C14···C2x3.447 (7)H12B···H112.2715
C14···N13.408 (6)H12B···Br1i2.7874
C14···C63.443 (7)H17A···H112.2297
C15···C6x3.544 (7)H17B···C7v3.0551
C15···C73.561 (8)H17C···Br13.0631
C15···C63.464 (7)H18A···H12Aviii2.5949
C16···C53.513 (7)H18B···H5A2.4512
C16···C5x3.494 (7)H18C···O1Wv2.8945
C16···C4x3.479 (7)
H1A—O1W—H1B105.97C14—C18—H18B109.42
C12—N11—C16122.0 (4)C14—C18—H18C109.42
C12—N13—C14117.2 (4)C14—C18—H18A109.44
C12—N11—H11119.08H18A—C18—H18B109.50
C16—N11—H11118.90H18B—C18—H18C109.51
H12A—N12—H12B120.02H18A—C18—H18C109.55
C12—N12—H12A119.95N1—C2—N3125.3 (4)
C12—N12—H12B120.03N2—C2—N3117.2 (4)
C2—N1—C6116.4 (4)N1—C2—N2117.5 (4)
C2—N3—C4116.8 (4)N3—C4—C5121.7 (4)
H2A—N2—H2B119.97N3—C4—C8117.0 (4)
C2—N2—H2A119.99C5—C4—C8121.4 (4)
C2—N2—H2B120.05C4—C5—C6118.2 (4)
N12—C12—N13119.6 (4)N1—C6—C7116.7 (4)
N11—C12—N13121.6 (4)C5—C6—C7121.8 (5)
N11—C12—N12118.8 (4)N1—C6—C5121.5 (4)
N13—C14—C15122.7 (4)C6—C5—H5120.85
N13—C14—C18115.7 (4)C4—C5—H5120.92
C15—C14—C18121.6 (4)C6—C7—H7A109.43
C14—C15—C16119.2 (4)C6—C7—H7B109.43
C15—C16—C17126.3 (4)H7A—C7—H7B109.53
N11—C16—C17116.4 (4)H7A—C7—H7C109.53
N11—C16—C15117.3 (4)C6—C7—H7C109.43
C14—C15—H5A120.43H7B—C7—H7C109.48
C16—C15—H5A120.37C4—C8—H8B109.49
C16—C17—H17B109.40C4—C8—H8C109.46
C16—C17—H17A109.49C4—C8—H8A109.42
H17A—C17—H17B109.53H8A—C8—H8C109.48
C16—C17—H17C109.43H8B—C8—H8C109.45
H17B—C17—H17C109.52H8A—C8—H8B109.53
H17A—C17—H17C109.46
C16—N11—C12—N12178.1 (4)C4—N3—C2—N2178.9 (4)
C16—N11—C12—N131.6 (6)C4—N3—C2—N12.5 (6)
C12—N11—C16—C150.0 (6)C2—N3—C4—C51.2 (6)
C12—N11—C16—C17178.7 (4)C2—N3—C4—C8178.6 (4)
C14—N13—C12—N111.1 (6)N13—C14—C15—C162.5 (7)
C14—N13—C12—N12178.6 (4)C18—C14—C15—C16177.1 (4)
C12—N13—C14—C150.9 (6)C14—C15—C16—N112.0 (6)
C12—N13—C14—C18178.7 (4)C14—C15—C16—C17176.6 (4)
C2—N1—C6—C7178.4 (4)C8—C4—C5—C6179.4 (4)
C6—N1—C2—N2179.9 (4)N3—C4—C5—C60.8 (6)
C2—N1—C6—C50.6 (6)C4—C5—C6—N11.7 (7)
C6—N1—C2—N31.6 (6)C4—C5—C6—C7177.2 (4)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1; (iii) x, y+1, z+1; (iv) x, y, z1; (v) x+1, y+1, z+1; (vi) x, y, z+1; (vii) x, y, z+2; (viii) x+1, y, z+2; (ix) x1, y, z; (x) x+1, y, z; (xi) x+1, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1A···Br10.802.683.471 (6)170
O1W—H1B···N1iii0.802.062.848 (6)169
N2—H2A···N3vii0.862.193.045 (6)175
N2—H2B···O1Wvi0.862.182.926 (6)145
N11—H11···Br1i0.862.413.248 (5)164
N12—H12A···N13viii0.862.132.993 (6)177
N12—H12B···Br1i0.862.793.537 (5)147
Symmetry codes: (i) x+1, y, z+1; (iii) x, y+1, z+1; (vi) x, y, z+1; (vii) x, y, z+2; (viii) x+1, y, z+2.
 

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